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Moisture-curable polysiloxane coating composition

a technology of polysiloxane and composition, applied in the direction of coatings, etc., can solve the problems of difficult to obtain the good balance between these properties, slow or incomplete cure, and difficulty in processing materials without risking premature gelation, etc., to achieve rapid cure, effective cure, and catalyze the effect of polysiloxane composition

Active Publication Date: 2015-11-03
3M INNOVATIVE PROPERTIES CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The patent text describes a curable polysiloxane composition that can cure quickly and without the need for heat or mixing of two parts. The composition uses a specific base catalyst that is stable in solution and can be used in low concentrations. The composition is stable in solution for a long time and can be used in sensitive applications without leaving any catalyst contamination. The technical effects of this composition include efficient processing, low-temperature curing, and environmental friendliness.

Problems solved by technology

A good balance between these properties is often difficult to obtain, as rapid reactivity and storage stability are opposite properties to each other.
For example, highly active catalysts such as tetraalkyl titanate esters rapidly accelerate the moisture-curing reaction but, at the same time, can make it difficult to process the materials without risking premature gelation in feed tanks, coating equipment, and other manufacturing and handling apparatus.
Control of the amount of moisture can be critical, with too little moisture potentially resulting in slow or incomplete cure and too much moisture resulting in premature cure.
While this approach has been useful in small-scale applications, it has been less efficient for large-scale manufacturing, where delays caused by having to mix the two parts have been undesirable.
Furthermore, coating operations must be completed expeditiously before the composition cures in the pot, and this has been difficult when working with large surface area substrates or a large volume of composition.
In addition, the heat used to activate the catalyst can damage heat-sensitive substrates onto which the composition has been applied.
Such materials have not required heat activation and therefore have enabled the use of heat-sensitive substrates without damage (and without the production of undesirable species requiring removal), but the materials have been relatively expensive, have exhibited cure inhibition on some substrates, and have required moisture control and the use of coating equipment with irradiation capability.
The compositions have been widely used for pressure-sensitive adhesive and mold release applications but have sometimes suffered from relatively short pot lives.
In addition, the use of tin catalysts is becoming particularly problematic because the organotin compounds generally employed as catalysts are now considered to be toxicologically objectionable.

Method used

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  • Moisture-curable polysiloxane coating composition
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Examples

Experimental program
Comparison scheme
Effect test

example 2

Preparative Example 2

PE-2

Preparation of HFPO-Derived Alcohol from HFPO-Derived Methyl Ester F(CF(CF3)CF2O)aCF(CF3)CH2OH, MN=1350

[0147]The alcohol was prepared by reduction of the methyl ester prepared as described above in PE-1, with sodium borohydride in a NOVEC™ 7100 / tetrahydrofuran solvent system, essentially by the method described in Preparative Example 2 of U.S. Patent Application No. 61 / 559,762 (Flynn et al., filed Nov. 15, 2011), which method is incorporated herein by reference.

example 3

Preparative Example 3

PE-3

Preparation of HFPO-Derived Allyl Ether from HFPO-Derived Alcohol F(CF(CF3)CF2O)aCF(CF3)CH2OCH2CH═CH2, MN=1420

[0148]The allyl ether was prepared by reaction of the alcohol prepared as described above in PE-2, with allyl bromide in NOVEC™ 7200 solvent in the presence of potassium hydroxide, water, and tetrabutylammonium bromide, essentially by the method described in Preparative Example 2 of U.S. Patent Application No. 61 / 559,762 (Flynn et al., filed Nov. 15, 2011), which method is incorporated herein by reference.

[0149]In the following Preparative Examples, either 1,3-bis(trifluoromethyl)benzene or 1,4-bis(trifluoromethyl)benzene could be used interchangeably.

example 4

Preparative Example 4

PE-4

Preparation of Reaction Product of HFPO-Derived Allyl Ether with HMS-991 (1 Percent Equivalent Loading of Allyl Ether to Siloxane)

[0150]HMS-991 (20 g, 0.298 eq) and HFPO-derived allyl ether (prepared as described above in PE-3, MN=1420, 4.23 g, 0.003 eq) were placed in a 100 mL round bottom flask with 1,4-bis(trifluoromethyl)benzene (60 mL, obtained from Alfa Aesar, Ward Hill, Mass.), and the resulting mixture was heated. When the temperature of the mixture reached about 50° C., platinum hydrosilation catalyst [platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex, solution in xylenes (approximately 2 weight percent platinum, obtained from Aldrich Chemical Company, Milwaukee, Wis.)] (0.05 g) was added to the mixture, and the resulting composition was heated to 60° C. for 16 hours. At the end of this time, solvent was stripped from the composition via rotary evaporation at 55° C. and a reduced pressure of 15 torr (1.60 kPa). The H-NMR spectrum of the ...

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Abstract

A moisture-curable polysiloxane composition consists essentially of (a) at least one polyorganosiloxane, fluorinated polyorganosiloxane, or combination thereof comprising reactive silane functionality comprising at least one hydrosilyl moiety; and (b) at least one base selected from amidines, guanidines, phosphazenes, proazaphosphatranes, and combinations thereof; wherein the curable composition is non-foaming and has an average condensation-curable, reactive silane functionality greater than two.

Description

CROSS REFERENCE TO RELATED APPLICATIONS[0001]This application is a national stage filing under 35 U.S.C. 371 of PCT / US2013 / 046072, filed Jun. 17, 2013, which claims priority to U.S. Provisional Patent Application No. 61 / 665,146, filed Jun. 27, 2012, the disclosures of which are incorporated by reference in their entirety herein.STATEMENT OF PRIORITY[0002]This application claims the priority of U.S. Provisional Application No. 61 / 665,146, filed Jun. 27, 2012, the contents of which are hereby incorporated by reference.FIELD[0003]This invention relates to curable coating compositions comprising reactive silane functionality and, in other aspects, to processes for coating the compositions and articles prepared thereby.BACKGROUND[0004]Moisture-curable polysiloxane compositions cure in the presence of moisture to form crosslinked materials such as release coatings and surface treatments that are useful in many industries. For example, a polysiloxane or fluorinated polysiloxane is often se...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C09D183/04C08G77/08C09D183/08C08G77/12C08K5/5399C08G77/04C08K5/29C08K5/31
CPCC09D183/04C08G77/08C09D183/08C08K5/29C08K5/31C08K5/5399C08G77/045C08G77/12
Inventor BUCKANIN, RICHARD S.FLYNN, RICHARD M.
Owner 3M INNOVATIVE PROPERTIES CO
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